On the IUPAC nomenclature of ethers and esters

  • Thread starter fakecop
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Hello,

I was wondering if there is a systematic procedure to follow when naming complex organic molecules containing ethers and esters. By "complex" I mean organic molecules that contain multiple ether/ester groups and possibly within multiple different branches of the molecule.

1.How to determine the alkoxy/alkyl groups when there are multiple ether linkages in the molecule?
E.g. CH2---O---CH2CH3CH2---O---CH3CH2CH2---O---CH2

-Similarly, how to name the alkyl group when there are multiple ester groups in the molecule?
E.g. CH3---COO---CH2CH3CH2---COO---CH3


2.How to name the alkoxy group when it contains an aldehyde or carboxylic acid?
E.g. COOH---CH2---O---CH2---COOH
I'm guessing that I'd have to switch to prefix notation, so the compound above would be called
"2-carboxymethoxyethanoic acid" or "dicarboxymethyl ether"?

If that is the case, how would you name the ether if the carboxyl/oxo group is directly attached to the Oxygen, like this:
COOH --O -- COOH or CHO --O --CHO ?

3. How do you name aldehydes/carboxylic acids joined by an ester?
E.g. CHO---CH2---COO---CH2---COOH
So now do I have to switch to prefix form for both groups? Thus, would this molecule be named
"carboxylmethyl 3-oxopropanoate"?

My textbook and most sources on the internet only covers the simple stuff. Please help me.
(I apologize for the messy diagrams but there is no LaTex symbols for organic chemistry)
 

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